Dimethyl Sulfate → N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine

HRID 240557

反応式

HRID 240557 の反応式
[OH-].[Na+].[CH3:3][C:4]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1.S(OC)(O[CH3:28])(=O)=O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>O.C1(C)C=CC=CC=1>[CH3:28][NH:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:4]=2[CH3:3])=[CH:8][C:9]=1[N+:14]([O-:16])=[O:15]

参加物

7

反応物 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 11433187Bis(tetrabutylammonium) sulphateHCID 866508954-(2-Methyl-4-nitrophenoxy)-2-nitrobenzenamine

生成物 1

HCID 86650896N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine収率 91%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a solution of sodium hydroxide (10.2 g in 10.5 mL water) was added toluene (15 mL), 4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine (2.00 g, 6.92 mmol), dimethyl sulfate (750 μL, 7.88 mmol) and tetrabutylammonium sulfate (0.277 g, 0.816 mmol). After stirring at room temperature, the cooled (0° C.) reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (100 mL). The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was chromatographed (dichloromethane) to provide the product (1.90 g, 91%).

後処理

  1. temperaturethe cooled
  2. custom(0° C.) reaction mixture
  3. extractionextracted with dichloromethane (100 mL)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (dichloromethane)

出典と根拠

ORDレコード
ord-84b6540a481e4829af7f3db48c89bdc2
出典データセット
uspto-grants-2014_02
特許番号
US08648087B2

関連ノート

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